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Comparison of Chlorine Dioxide and Ozone As Oxidants for the Degradation of Volatile Organic Compounds

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Comparison of Chlorine Dioxide and Ozone As Oxidants for the Degradation of Volatile Organic Compounds Comparison of Chlorine Dioxide and Ozone as Oxidants for the Degradation of Volatile Organic Compounds by Md Abdul Hoque A Thesis Submitted in Partial Fulfillment of the Requirements for the Degree of Master of Science in Chemistry Middle Tennessee State University August 2018 Thesis Committee: Dr. Ngee Sing Chong, Research advisor Dr. Chengshan Wang Dr. Mengliang Zhang ACKNOWLEDGEMENTS I would like to express my sincere gratitude to the people who supported me as I completed this journey during my academic period here in Middle Tennessee State University. First, I would like to thank my research supervisor Dr. Ngee Sing Chong, who supported me from the very beginning to the end with his patience. His continuous guidance helped me to learn and finish this thesis work today. I am also very thankful to Dr. Chengshan Wang and Dr. Mengliang Zhang who were in my thesis committee. I appreciate their efforts and spending valuable time in reviewing my thesis. I am thankful to Jessie Weatherly for his assistance to solve all the instrumental problems during my project. A very special thanks to my parents and siblings for their love and encouragement. I would also like to thank my friends at MTSU, and lab mates for their help and support. Finally, I wanted to thank to MTSU Chemistry Department and all the faculty members for their support. ii ABSTRACT The presence of hazardous volatile organic compounds (VOCs) in both indoor and outdoor air is a grave issue in environmental pollution. The exposure of these compounds may cause chronic disease or adverse effects in humans. The major sources of these toxic compounds are due to improper waste disposal by chemical manufacturers, waste stream from food processing, industrial sources, and decay of living cells. Therefore, the reduction of VOCs by oxidative reactions is the primary goal of this thesis project. Both chlorine dioxide and ozone are used to evaluate the degradation characteristics of dimethyl trisulfide, isoprene, 1-bromopropane, 2,3-butanedione, and 1,1,2-trichloroethane. Gas chromatography coupled to mass spectroscopy (GC-MS) and Fourier Transform infrared spectrometry (FTIR) were used to characterize the gas phase reaction products of these compounds. The results show that dimethyl trisulfide and isoprene were substantially degraded into other by-products, including methane sulfonyl chloride and sulfur dioxide, during oxidation by chlorine dioxide and ozone, respectively. In contrast, 1-bromopropane, 2,3- butanedione and 1,1,2-trichloroethane have slow reaction kinetics and did not break down completely. Degradation of dimethyl trisulfide by chlorine dioxide and ozone follows the second order kinetics with half-lives of 2.2 min and 24 min, respectively. On the other hand, isoprene follows the first order reaction kinetics with rate constants of 0.4051 min-1 and 0.02244 min-1 and half-lives of 1.73 min and 32 min for degradation using ozone and chlorine dioxide, respectively. iii The oxidative degradation of 1-bromopropane, dimethyl trisulfide, and 2,3- butanedione by chlorine dioxide were more efficient than their reactions with ozone. However, the degradation of isoprene and 1,1,2-trichloroethane showed a greater reactivity toward ozone compared to chlorine dioxide. Most of the reaction products of oxidative degradation such as acetone, ethanol, formic acid, and dimethyl ether are chemically benign. But there are also by-products such as methane sulfonyl chloride, sulfur dioxide, chloroform, and cyanogen bromide that require further toxicological study. iv TABLE OF CONTENTS Page 1 INTRODUCTION ....................................................................................................... 1 1.1 Environmental pollution ....................................................................................... 1 1.2 Air pollution ......................................................................................................... 1 1.3 Selected harmful or malodorous compounds ....................................................... 3 1.3.1 1-Bromopropane ........................................................................................... 4 1.3.2 Dimethyl trisulfide ........................................................................................ 5 1.3.3 2,3-Butanedione ............................................................................................ 6 1.3.4 Isoprene ......................................................................................................... 6 1.3.5 1,1,2-Trichloroethane .................................................................................... 7 1.4 Ozone overview.................................................................................................... 7 1.4.1 Properties of ozone ....................................................................................... 7 1.4.2 Ozone generation method ............................................................................. 7 1.4.3 Application of ozone ..................................................................................... 9 1.4.4 Formation of ozone by-products ................................................................. 10 1.5 Chlorine dioxide overview ................................................................................. 11 1.5.1 Properties of chlorine dioxide ..................................................................... 11 1.5.2 Chlorine dioxide generation method ........................................................... 11 1.5.3 The application of chlorine dioxide ............................................................ 12 1.5.4 Chlorine dioxide disinfectant by-products (DBPs) ..................................... 13 1.6 Thesis proposal ................................................................................................... 13 v 2 MATERIALS AND METHODS .............................................................................. 15 2.1 Materials and chemical reagents ........................................................................ 15 2.2 Production of ozone ........................................................................................... 15 2.3 Generation of chlorine dioxide gas .................................................................... 16 2.4 Canister cleaning system .................................................................................... 18 2.5 Methods for analytical measurements ................................................................ 19 2.5.1 Sample preparation for GC-MS and FTIR analysis .................................... 19 2.5.2 GC-MS measurements ................................................................................ 20 2.5.3 FTIR analysis .............................................................................................. 21 3 RESULTS AND DISCUSSIONS ............................................................................. 23 3.1 GC-MS and FTIR analysis of air pollutants by ozone ....................................... 23 3.1.1 Degradation of dimethyl trisulfide with chlorine dioxide ........................... 23 3.1.2 Degradation of dimethyl trisulfide by ozone .............................................. 27 3.1.3 Degradation of 1-bromopopane with chlorine dioxide ............................... 31 3.1.4 Degradation of 1-bromopropane with ozone .............................................. 35 3.1.5 Degradation of isoprene with chlorine dioxide ........................................... 39 3.1.6 Degradation of isoprene with ozone ........................................................... 42 3.1.7 Degradation of 2,3-butanedione with chlorine dioxide .............................. 45 3.1.8 Degradation of 2,3-butanedione with ozone ............................................... 48 3.1.9 Degradation of 1,1,2-trichloroethane with chlorine dioxide ....................... 51 3.1.10 Degradation of 1,1,2-trichloroethane with ozone ....................................... 53 3.1.11 Degradation kinetics study of selected compounds with chlorine dioxide by FTIR analysis ............................................................................................................ 56 vi CONCLUSION...........................................................................................................60 REFERENCES ...........................................................................................................62 APPENDIX ............................................................................................................... 65 vii LISTS OF FIGURES Page Figure 1: Setup for the production of ozone from pure oxygen ..................................... 16 Figure 2: Generation of chlorine dioxide gas using precursors ....................................... 18 Figures 3: Comparison of FTIR spectra of treated dimethyl trisulfide by chlorine dioxide at different time interval ................................................................................................... 24 Figure 4: FTlR spectral changes of chlorine dioxide after treatment of dimethyl trisulfide samples .............................................................................................................................. 24 Figure 5: Plots showing decreasing concentration of dimethyl trisulfide and chlorine dioxide as a function of their reaction time at room temperature ..................................... 25 Figure 6: GC-MS overlay chromatograms of treated and untreated dimethyl trisulfide. 27 Figure 7: Comparison of FTIR
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